Deuterated Oxytocins: The Synthesis and Biological Properties of a Crystalline Analog of Deamino-oxytocin Deuterated in the 5-asparagine Position

This paper describes the synthesis and biological activity of [5-L-asparagine-α ,β ,β -d3]-deamino-oxytocin. The model peptide S-benzyl-β -mercaptopropionyl-L-asparaginyl-α ,β ,β -d3-glycinamide was also prepared to observe the effect of the conditions of peptide synthesis on the deuterium content....

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Bibliographic Details
Published in:Proceedings of the National Academy of Sciences - PNAS 1969-09, Vol.64 (1), p.263-266
Main Authors: Blomquist, Alfred T., Rich, Daniel H., Carlson, Bruce A., Allen, G. Ashley, Hruby, Victor J., Takashima, Herbert, Nangeroni, Louis L., Glose, Paula, Du Vigneaud, Vincent
Format: Article
Language:English
Subjects:
Acetates
Amino Acid Sequence
Amino acids
Animals
Asparagine
Atoms
Biochemistry
Biological Sciences: Biochemistry
Chickens
Deuterium
Esters
Ethers
Models, Chemical
Oxytocics
Oxytocin - chemical synthesis
Oxytocin - pharmacology
Spectrophotometry
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Summary:This paper describes the synthesis and biological activity of [5-L-asparagine-α ,β ,β -d3]-deamino-oxytocin. The model peptide S-benzyl-β -mercaptopropionyl-L-asparaginyl-α ,β ,β -d3-glycinamide was also prepared to observe the effect of the conditions of peptide synthesis on the deuterium content. It was found that normal synthetic procedures could be used without a significant loss in the deuterium content. The [5-L-asparagine-α ,β ,β -d3]-deamino-oxytocin had, within experimental error, the same avian vasodepressor and oxytocic activities as deamino-oxytocin itself.
ISSN:0027-8424
1091-6490
DOI:10.1073/pnas.64.1.263